How to know if a friendship is good for your kid or not

I have 4 kids and most of them have a lot of friends except my 16 year old. We've had some issues with bullies. And my daughter graduated last year so my 16 year old son had no one to start the school year with. He has started hanging out with a kid and it seems they're becoming close. My husband and my dad have two very different perspectives on this friend. His name is Daniel. We've known him since my son was in 5th grade. Honestly imagine this. You're dropping your 5th grader off for the first day and the first kid in class is a 10 year old boy wearing hello kitty ear rings. A pink skirt with pink nails chewing gum. Daniel is a character. I've met his parents and they just encouraged their kid to be himself. He sometimes dresses like a regular boy. Other times dresses very feminine. My parents have met him last year at the fall carnival which is why they aren't the biggest fans of him. What happened was he was wearing a skirt with boots and my mom asked his mom why she allowed that and she said because he likes it. My mom told his mom she would never let her son dress like that and he needs to know that's for girls. Daniel said "I've been told that. I didn't know I needed a pussy to wear a skirt. My cock fits in my skirt just fine thank you." My husband almost pissed himself laughing. My dad thinks him getting close with Daniel will ruin and confuse him. My husband thinks my son needs a friend like Daniel because Daniel is unapologetically himself. My husband told me a time where he was subbing at the high stand Daniel was getting picked on but the boys trying to bully him were getting mad that he was so unbothered and that's the example he needs in his life. He remembers Daniel telling the bully (because the bully called him a f@g. I think Daniel is bi) that he may be a f@g but at least the bullies girlfriend doesn't have to fake her orgasm with him(Jesus). My husband thinks this new friendship is great. My parents don't. Honestly all I want is my kids to have good friends who are good influences in their life. I don't hate Daniel. Honestly I've had some conversations with him and his parents and behind the sass he's a sweet boy who's had a difficult life. I do think he's helping my son come out of his shell more. My son likes to sing but has stage fright and Daniel sings too. He has gotten my son to sing more publicly and gotten my son addicted to punk music. I think my parents fears are that my son will be feminized hanging out with him or something. But for once none of my kids are lonely.